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I'm thinking more when they get older though. I think most punk bands music dropped off when they got older. With Green Day they were probably very early 20's when they released Insomniac (agree that's their best record).
The guys I would argue maybe did evolve as they got older would be John Lydon with PiL and Ian Mackaye with Fugazi but idk if Sex Pistols and Minor Threat fans followed them.
What about Aerosmith? Steve Tyler was about 25 when Dream On came out and 50 when Jaded/Don't Want to Miss a Thing were big.
I believe country artist George Strait had 30 years in between his first and last #1 hits. Although country singers kind of don't count because they don't normally write all their own stuff.
Seems like most musicians have about a 10 year period where they can be in their prime. Some shorter, some a little longer. Most bands that hang on for too long just wind up making really bland and boring music in their older years. I'm not sure if they do it for themselves because it's just what they've always done and they enjoy it or if they really think that they're going to recapture the magic they once had? They wind up being equivalent to Rick Flair trying to wrestle with his flabby old man body in his 70s. Not a good look.